Dearomative Addition of Carboranyl Anions to Isoquinolinium Salts and Subsequent Reduction to Access Carborane‐Functionalized Dihydroisoquinolines

IF 2.8 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry Pub Date : 2024-09-05 DOI:10.1002/ajoc.202400390

Yun-Fan Gao, Chen-Ming Xu, Ming-Hui Yu, Yongna Zhang, Xiao-Jun Wu, You-Qing Wang

引用次数: 0

Abstract

A dearomative addition of readily available carboranyllithium reagents to isoquinolinium salts gave a series of carborane cage C‐substituted 1,2‐dihydroisoquinolines in 43−85% yields. Subsequent hydrogenation enabled the facile synthesis of corresponding carboranyl 1,2,3,4‐tetrahydroisoquinolines in 65−95% yields. The addition‐reduction pathway is applicable to a wide range of substituted isoquinolinium salts and o‐carborane or m‐carborane.

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硼烷阴离子与异喹啉鎓盐的亲和性加成及随后的还原反应，以获得硼烷官能化的二氢异喹啉

将容易获得的硼烷基锂试剂与异喹啉盐进行脱芳加成，可得到一系列硼烷笼 C 取代的 1,2-二氢异喹啉，收率为 43-85%。随后的氢化反应使相应的 1,2,3,4-四氢异喹啉的硼烷合成变得容易，产率达到 65-95%。加成-还原途径适用于多种取代的异喹啉盐和邻硼烷或间硼烷。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Asian Journal of Organic Chemistry CHEMISTRY, ORGANIC-

CiteScore

4.70

自引率

3.70%

发文量

372

期刊介绍： Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC) The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.